Vayira Yaakov me'od vayeitzar lo (32:7)

The Torah relates that upon hearing that Eisav was coming toward him with 400 men, Yaakov became very frightened and it distressed him. Rashi explains that the double expression regarding Yaakov's fear teaches that he was afraid both that he may be killed and that he may kill others should Eisav attack him. It is natural to understand why Yaakov would be afraid of being killed. However, as the law is (Sanhedrin 72a) that one may kill a pursuer in self-defense, why was he afraid of killing others?

The Maharil Diskin answers by citing Rashi, who writes (27:45) that Rivkah prophetically declared that her two sons - Yaakov and Eisav - would both die on the same day. As a result, Yaakov was afraid that if he was attacked, he may end up killing Eisav, which would lead to his immediate death.

Based on this explanation, the Maharil Diskin resolves another difficulty. Yaakov split his family and possessions into two camps and expressed confidence that even if Eisav would destroy one camp, the remaining one would surely survive (32:8). If Yaakov feared that Eisav may indeed prevail over his first camp, why was he so sure that the second camp wouldn't also succumb? Rav Yehoshua Leib explains that Yaakov placed a distance of one day's travel between the two camps and positioned himself at the front of the first camp. As a result, he was certain that even if he was killed, Eisav would also die on that day before having an opportunity to reach the second camp, thereby guaranteeing its survival.

Katonti mikol ha'chasadim (32:11)

Hashem promised to protect Yaakov and return him safely to the land of Canaan. Nevertheless, as he prepared to face his brother Eisav who was approaching him with an army of 400 men, Yaakov became very frightened. Why wasn't he confident that Hashem would protect and save him in fulfillment of His promise? Rashi explains that Yaakov feared that perhaps the miracles Hashem performed for him after the promise him had depleted his supply of merits. We find in the Torah that the way of the righteous is one of humility, never requesting anything in their own merits, but always relying on Hashem's infinite mercy and kindness to give them gifts that they feel they don't really deserve. This makes it puzzling to observe Yaakov worrying that the miracles that Hashem did for him were payment for his merits, and he may therefore not have any remaining.

The Vilna Gaon explains that there is a difference between Divine acts of kindness which have already been done and those that a person would like to be performed. With respect to the future, a person should indeed not rely upon his accumulated merits. If he wants to have his wishes fulfilled, he should throw himself on Hashem's mercy. Regarding the past, however, a sense of humility should cause a person to worry that the few merits that he may have possessed were used up by the numerous Heavenly gifts that he has received.

In light of this explanation, the Vilna Gaon brilliantly explains a cryptic comment made by the Gemora in Sotah (5a). The Gemora teaches that a Torah scholar should have one-eighth of one-eighth of arrogance. It is difficult to understand why conceit would ever be appropriate, and why was this seemingly arbitrary measurement selected as the appropriate amount? The Gaon points out that Parshas Vayishlach is the eighth portion in the Torah, and ours is the eighth verse in the parsha. The Gemora is hinting that the only acceptable form of arrogance is that described in our verse, namely the concern that whatever merits one may have had have already been used up.

Vatigashna ha'shefachos heina v'yaldeihen vatishtachavena vatigash gam Leah v'yaldeha vayishtachavu v'achar nigash Yosef v'Rochel vayishtachavu (33:6-7)

The Torah records that just before his climactic meeting with Eisav, Yaakov arranged his wives and their children, placing first the maidservants and their sons, then Leah and her children, and finally Rochel and her son Yosef. Although this may indeed have been a logical plan, it seems to contradict Yaakov's initial strategy. In the beginning of the parsha, Yaakov prepared for war and divided his family into two camps, placing a distance of one day's travel between them so that at least some of them would survive (32:8-9). When he finally encountered Eisav, why were all of his wives and children present, and why did he abandon his original plans?

The Matamei Yaakov answers that after Yaakov wrestled with Eisav's guardian angel and emerged triumphant, he was no longer afraid of Eisav and abandoned his previous plans as no longer necessary. Yaakov's newfound confidence can be better understood in light of an insight of the Brisker Rov. Eisav's angel informed Yaakov (32:29) that because he had successfully wrestled with Hashem and with men, his name would be changed to Yisroel. Rashi explains that "with men" refers to his victories over Lavan and Eisav. How could the angel tell Yaakov that he had triumphed over Eisav when he had yet to even encounter him in person?

The Medrash says that the dust which was kicked up from the clash between Yaakov and Eisav's angel ascended all the way to Hashem's Throne of Glory. The Brisker Rov explains that the Medrash isn't relating a trivial fact about the location of the dust. It is coming to teach that this was no mundane wrestling match, but rather a battle which was being fought in Heaven. If so, once Yaakov had emerged victorious from his celestial duel, it was already a foregone conclusion that he would be successful in his earthly encounter with Eisav. In light of this explanation, it is easy to understand why Yaakov scrapped his initial military scheme, for he was now secure that he had nothing to fear.

Vateiled Rochel vat'kash b'lidta (35:16)

In relating the difficulties involved in Binyomin's birth, the Torah records that Rochel gave birth and subsequently had difficulties with the childbirth. This chronology of events isn't what we would expect. In a regular birth, first a woman has labor pains, and then the child is born, but when Rochel gave birth to Binyomin the order was reversed. Why did her pains begin only after she had already given birth?

The Chida answers that the Mishnah in Shabbos (2:6) teaches that women die during childbirth for being lax in one of 3 areas: the separation of challah, the laws of family purity, and lighting Shabbos candles. When Rochel's delivery of Binyomin was abnormally difficult, she feared that perhaps she might die. Additionally, she also feared that people who heard she died during childbirth would assume that it was because she had sinned in one of these three areas and wasn't as righteous as she was alleged to be.

In reality, the Mishnah is specifically referring to those who die during the time of danger (Shabbos 32a), which is limited to the actual childbirth, and not to a person (such as Rochel) who has post-delivery complications. However, the Torah continues by noting that even after the baby was born, Rochel's pain continued to intensify, and with it her fears about the implications.

At this point, Rochel's midwife attempted to comfort her by explaining the aforementioned difference: "Vatomer la ham'yaledes al tir'i ki gam zeh lach ben." In other words, don't be afraid of what people will say because your son has already been born, in which case even if you die, it will no longer be due to the sins mentioned in the Mishnah. Still, Rochel wasn't persuaded by this logic and called her child "Ben oni" - "son of my affliction" - as she felt that even a woman who dies from immediate post-labor complications is also included in those referred to by the Mishnah. Yaakov, however, knew the truth about Rochel's righteousness and called the child "Ben yemin" - the son of the right, which is always the stronger side - as a reference to her pious ways.

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Parsha Points to Ponder (and sources which discuss them):

1) Before his encounter with Eisav, Yaakov arranged his wives and their children, placing the maidservants and their sons first, then Leah and her children, and finally Rochel and her sons (33:2). Rashi explains that the more beloved to Yaakov they were, the closer to the back he placed them to protect them from Eisav. In Parshas Vayeishev, Yosef's brothers became jealous of him due to an extra article of clothing he received from Yaakov (37:4). Why didn't they similarly become jealous here, when their being placed closer to the front than Yosef could potentially be life-threatening? (Meged Yosef)

2) After Sh'chem and his father attempted to convince Yaakov and his sons to allow Sh'chem to marry Dina and offered their daughters in marriage to the brothers, Yaakov's sons answered and explained that they could only do so if Sh'chem and his townsmen would circumcise themselves (34:13-17). As Rashi writes (24:50) that Lavan demonstrated his wickedness by speaking up before his father Besuel and not allowing his father to answer, why did the brothers answer in front of their father Yaakov? (Tosefos Rid 24:50, Emes L'Yaakov)

3) Rashi writes (35:8) that the date of Rivkah's death was hidden so that people wouldn't curse the womb from which Eisav emerged. Why wasn't the date of Yitzchok's death concealed for the same reason, as he was Eisav's father? (Gur Aryeh, Ayeles HaShachar)

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